The Sunshine Skyway Bridge provides a breathtaking watery view of Tampa Bay. It also acts as a marker, indicating you’re not too far from Gulfport, a relaxed town that extends for all of four miles. In its earliest days, there was no beach, but gradually sea walls were built and the mud flats were filled in. Today, with its flocks of gulls on the sand, warm balmy breezes and swing-set-style park benches, this sleepy suburb of St. Petersburg is a mere smidge of a city. It’s seated on Boca Ciega Bay where a two-story pavilion — the town’s first casino — was built on the end of the historic Williams Pier in 1906. The legacy of casinos in Gulfport is strong. Its third casino, built in the mid-1930s, has since become a refurbished 1920s-style ballroom with dockage for anyone arriving by boat for an evening of dining, dancing or both. In fact, ballroom dancing at the Gulfport Casino has become so popular it’s held five nights a week.
Culture and the arts draw creative types of all sorts to this “gateway to the Gulf.” Three professional theater troupes perform at the Catherine Hickman Theater. Traveling musician and actor Carl Asch has called Gulfport his home base on and off for 20-plus years. Sunday mornings, you’ll find him at Pia’s Trattoria, his head deep into the New York Times crossword puzzle over brunch. His Celtic band, Empty Hats, often performs at the historic Peninsula Inn & Spa.
With no parking meters (gasp! since when have you seen that?) and its very own trolley that connects to St. Pete Beach, Gulfport, which celebrated its centennial last year, welcomes visitors. Tuesday is big here. It’s when the Gulfport Fresh Market happens — come rain or shine. The year-round market takes over a chunk of Beach Boulevard, the main drag of the Waterfront Arts District. Open-air booths pop up with nice folks selling everything from fresh produce, local honey and gourmet cupcakes to antiques and T-shirts with graphic peace signs. Tuesday is also a red-letter day in town because it’s when veteran blues man Sterling Magee performs at the Peninsula Inn & Spa with the Harlem Blues Band. Locals gather on the restaurant porch to listen to this 74-year-old musician once known as Five Fingers Magee.
Beach Boulevard also draws crowds on the first Friday and third Saturday of each month when Art Walk meshes entertainers and artists doing their thing under a star-filled sky. The stretch is also buzzing with shoppers. You won’t find any chain stores here, but rather a boulevard lined with boutiques. Anyone fond of memorabilia will love the vintage Gulfport signs at Bo-Tiki. Shoppers grin at the catchy sayings and illustrations straight out of the 1940s and ’50s that adorn the signs. On any given day, you’ll find boomer ladies at the boutique graciously sipping a glass of wine, offered by the store owner, as they sort through beach attire and jewelry. Naturally, purchases ensue.
A walkabout on Beach Boulevard reveals the town’s culinary hot spots, like Peg’s Cantina and Brewpub with garden seating. Its fresh Mexican fare pairs nicely with craft beers, including Peg’s G.O.O.D. on draft. Across the street, the aromas practically waft out the door at Pia’s Trattoria, with its pale yellow stucco-walled Sienna-style ambience. This is the place to order spaghetti Di Bologna, a brimming bowl of handcrafted pasta with the thickest, richest Bolognese sauce — so delicious it should be bottled. Continue to the end of the street and head toward the pier on Shore Boulevard for O’Maddy’s Bar & Grille. This local hangout epitomizes the “where everybody knows your name” vibe and serves up sandwiches like Kimberly’s Crabby Cake, a yummy backfin lump and claw crab cake on a pretzel bun with chipotle mayo. Vistas of the pier, with jumping mullets and the occasional bottlenose dolphin in the glistening bay, earn O’Maddy’s high marks for scenic appeal.
Places to stay overnight in Gulfport are as casual as the town, meaning you won’t find any over-the- top towering resorts here. When the Sea Breeze Manor was being sold back in 2002, it was exactly what Lori Rosso had been looking for. She left a high-powered West Wing D.C. career to bask in Gulfport’s ease. Now the president of the Gulfport Chamber of Commerce (her political chops make her perfect for the role), Rosso’s one of the area’s strongest advocates. “The optimum experience is to park and walk the streets so you can see all the charming bungalows and the artistic flair,” Rosso says. “Gulfport is a rarity,” she adds. Her sunny Sea Breeze Manor Bed & Breakfast, a rarity in its own right, sits across from the Boca Ciega Bay. Occasionally, the squawks of wild parrots flying past can be heard from the spacious 1923 vintage two-story home. Guest rooms, such as the deluxe Jamaica with its wraparound private porch, are appointed with kitschy antiques — including art deco floral-print settees. There’s a dog-friendly cottage too, for travelers who want to bring Fido along. A visit to the sleepy gem of Gulfport is about as authentically Old Florida as it gets.
“This unique community has a reputation for being the best-kept secret on the Gulf coast.” — Lori Rosso, InnKeeper, Sea Breeze Manor Bed & Breakfast
- Location — Gulfport is on Boca Ciega Bay, nestled between St. Petersburg and St. Pete Beach.
- Place to Stay — Sea Breeze Manor Bed & Breakfast
- Things to Do — Gulfport Fresh Market and Gulfport Art Walk
- Where to Eat — Pia’s Trattoria, Peg’s Cantina and Brewpub and O’Maddy’s Bar & Grille
- Shopping — Bo-Tiki and Lulu’s Tropical Beach Boutique
- Resources — Gulfport, St. Petersburg and Clearwater